Over the years, we’ve watched the Joker—DC Comics’ iconic supervillain—across film, television and literature. The character first appeared in the debut issue of the comic book Batman in 1940. Although he was planned to be killed off during his initial appearance, the Joker was spared by editorial intervention, allowing the character to endure as the archenemy of the superhero Batman.

In his comic book appearances, the Joker is portrayed as a criminal mastermind. Introduced as a psychopath with a warped sense of humor, the character became a goofy prankster in the late 1950s before returning to his darker roots during the early ’70s. The Joker has had various possible origin stories during his decades of appearances. The most common backstory involves him falling into a tank of chemical waste, with the resulting disfigurement driving him insane.

An antithesis of Batman in terms of personality and appearance, the Joker is considered by critics to be the caped crusader’s perfect adversary. He remains a timeless character in pop culture and is often listed among the all-time greatest comic book villains and fictional characters. He has been adapted in live-action, animated and video game media. As we count down the days until the release of Robert Pattinson’s turn as the Dark Knight with The Batman, here’s a closer look at our top-rated performances of the superhero’s archnemesis.

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5 Zach Galifianakis in The Lego Batman Movie (2017)

     Warner Bros. Pictures

There are big changes brewing in Gotham City, and if Batman wants to save the city from The Joker’s hostile takeover, he may have to actually work with others and learn to lighten up a bit. That’s the simple premise of The Lego Batman Movie, which hit theaters in the U.S. in 2017. The film received generally positive reviews from critics for its animation, voice acting, soundtrack, visual style and humor, and was also commercially successful, having grossed $312 million worldwide against a budget of $80 million.

MOVIEWEB VIDEO OF THE DAY

MOVIEWEB VIDEO OF THE DAY

MOVIEWEB VIDEO OF THE DAY

In person, Zach Galifinakis is perhaps best known for his scene-stealing supporting role in The Hangover movies as well as his starring turn as a literal clown in the FX series Baskets. His uniquely hilarious voice inflections complement The Lego Batman Movie perfectly; therefore, he earns a spot on this list.

4 Mark Hamill in Batman: The Animated Series (1992-94), other projects

     Warner Bros.

Hamill’s role as the Joker began in the 1992 series Batman: The Animated Series and continued to many later spin-off series, video games and films. Hamill received critical acclaim for his performance, which put him in high demand as a voice-over actor of cartoon villains.

“I wanted a part that was the polar opposite of Luke in every way,” Hamill tweeted earlier this year in reference to his iconic Star Wars character. “Something unexpected that would surprise people & show range & versatility. The Clown Prince of Crime was a gift from character-actor heaven.”

Hamill voiced the Joker in a handful of episodes of Batman: The Animated Series, along with multiple episodes of Superman: The Animated Series, The New Batman Adventures and Justice League, plus a few segments for Robot Chicken. He also voiced the Joker in the 1993 theatrical film Batman: Mask of the Phantasm and the 2000 direct-to-video film Batman Beyond: Return of the Joker.

Hamill also was praised for performance as the Joker in the animated version of Batman: The Killing Joke, which was released in theaters for a limited time in 2016. He has been nominated for two Annie Awards for his unique portrayal of the character, hence why he makes our list.

3 Jack Nicholson in Batman (1989)

Tim Burton’s megahit follows Gotham City crime boss Carl Grissom (Jack Palance) who effectively runs the town until a new crime fighter shows up: Batman (Michael Keaton). Grissom’s right-hand man is Jack Napier (Jack Nicholson), a brutal man who is not entirely sane. After a falling-out between the two, Grissom has Napier set up with the police, and Napier falls to his apparent death in a vat of chemicals. However, he soon reappears as The Joker and starts a reign of terror in Gotham City.

The darker version of the Joker made his film debut in 1989’s Batman, which earned over $400 million at the worldwide box office. The role was a defining performance in Nicholson’s career and was said by critics to overshadow Batman’s lead part. Batman’s success led to the 1992 television series, Batman: The Animated Series, which is where Hamill stepped in to shine as the supervillain. But Nicholson, the legendary Oscar winner, held the spotlight as the live-action version of the Joker for years to come.

2 Joaquin Phoenix in Joker (2019)

The most recent live-action film performance of the Joker is Arthur Fleck (Joaquin Phoenix), a working clown and aspiring stand-up comic. He has mental health issues, part of which involves uncontrollable laughter. Times are tough and, due to his issues and occupation, Arthur has an even worse time than most. Over time, these issues bear down on him, shaping his actions and making him ultimately take on the persona he is more known as.

The 2019 film from Todd Phillips focuses on the origins of the Joker in a much different light than previous installments in the Batman franchise. Although the film was controversial for its violence and portrayal of mental illness, Phoenix’s electrifying performance received widespread acclaim. Just like The Dark Knight before it, Joker grossed over $1 billion at the box office and earned numerous awards — including an Academy Award for Best Actor for Phoenix. Joker is the first live-action theatrical Batman film to receive an R-rating from the Motion Picture Association, but it succeeds with the freedom of an adults-only rating as it gave Phoenix free reign to let loose and utterly become a modern Joker.

1 Heath Ledger in The Dark Knight (2008)

     Via IMDb

Set within a year after the events of Batman Begins, The Dark Knight follows Batman (Christian Bale), Lt. James Gordon (Gary Oldman) and new DA Harvey Dent (Aaron Eckhart) who successfully begin to round up the criminals that plague Gotham City — that is, until a mysterious and sadistic criminal mastermind known only as “The Joker” appears in Gotham, creating a new wave of chaos. Batman’s struggle against The Joker becomes deeply personal, forcing him to “confront everything he believes” and improve his technology to stop him.

Considered one of the best films of its decade and one of the greatest and most influential films of all time, the film received critical acclaim for virtually all its components — screenplay, cirection, visual effects, musical score, cinematography and performances, particularly Ledger’s. With over $1 billion in revenue worldwide, it became the fourth-highest-grossing film at the time, and highest-grossing film of 2008; it also set the record for highest-grossing domestic opening with $158 million, a record it held for three years. At the 81st Academy Awards, the film received eight nominations, with Ledger posthumously awarded the Joker character’s first of two Oscars. While The Dark Knight’s Joker is a more supporting role than Phoenix’s 2019 turn, it is Ledger who carries Christopher Nolan’s best film to date. When asked early on why Ledger in particular was cast for the role, Nolan replied, “He’s fearless.”